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Evening Insurance Sales Jobs in Wisconsin (NOW HIRING)

If you are a sales PROFESSIONAL ready to be paid for your talents apply now and come join a team of ... insurance offering Schedule: - Flexibility on a weekly basis - Evening and weekend availability ...

If you are a sales PROFESSIONAL ready to be paid for your talents apply now and come join a team of ... insurance offering Schedule: - Flexibility on a weekly basis - Evening and weekend availability ...

If you are a sales PROFESSIONAL ready to be paid for your talents apply now and come join a team of ... insurance offering Schedule: - Flexibility on a weekly basis - Evening and weekend availability ...

If you are a sales PROFESSIONAL ready to be paid for your talents apply now and come join a team of ... insurance offering Schedule: - Flexibility on a weekly basis - Evening and weekend availability ...

Access to Direct Seller Perks including medical, dental, vision, and life insurance options,* and ... Availability for evening & weekend appointments * Direct Seller Contract * Deliver excellent ...

Outside Sales Representative

Madison, WI · On-site

$60K - $80K/yr

Access to Direct Seller Perks including medical, dental, vision, and life insurance options,* and ... Availability for evening & weekend appointments * Direct Seller Contract * Deliver excellent ...

Access to Direct Seller Perks including medical, dental, vision, and life insurance options,* and ... Availability for evening & weekend appointments * Direct Seller Contract * Deliver excellent ...

Outside Sales Representative

Kenosha, WI · On-site

$60K - $80K/yr

Access to Direct Seller Perks including medical, dental, vision, and life insurance options,* and ... Availability for evening & weekend appointments * Direct Seller Contract * Deliver excellent ...

Access to Direct Seller Perks including medical, dental, vision, and life insurance options,* and ... Availability for evening & weekend appointments * Direct Seller Contract * Deliver excellent ...

Access to Direct Seller Perks including medical, dental, vision, and life insurance options,* and ... Availability for evening & weekend appointments * Direct Seller Contract * Delivery of excellent ...

Outside Sales Representative

Madison, WI · On-site

$50K - $70K/yr

Access to Direct Seller Perks including medical, dental, vision, and life insurance options,* and ... Availability for evening & weekend appointments * Direct Seller Contract * Delivery of excellent ...

Access to Direct Seller Perks including medical, dental, vision, and life insurance options,* and ... Availability for evening & weekend appointments * Direct Seller Contract * Delivery of excellent ...

Access to Direct Seller Perks including medical, dental, vision, and life insurance options,* and ... Availability for evening & weekend appointments * Direct Seller Contract * Delivery of excellent ...

Access to Direct Seller Perks including medical, dental, vision, and life insurance options,* and ... Availability for evening & weekend appointments * Direct Seller Contract * Delivery of excellent ...

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Showing results 1-20

Evening Insurance Sales information

What is the difference between Evening Insurance Sales vs Day Insurance Sales?

AspectEvening Insurance SalesDay Insurance Sales
Work HoursPrimarily evenings and weekendsStandard daytime hours, typically 9am-5pm
Work EnvironmentOffice or remote, with flexible hoursOffice-based, regular business hours
Required CredentialsInsurance license, sales experienceInsurance license, sales experience
Industry UsageCommon in retail and direct sales settings

Both Evening Insurance Sales and Day Insurance Sales require similar credentials and industry knowledge. The main difference lies in work hours and environment, with evening roles offering flexibility for those who prefer or need to work outside traditional hours. Understanding these differences can help job seekers choose the schedule that best fits their lifestyle.

What are the most commonly searched types of Insurance Sales jobs in Wisconsin?

The most popular types of Insurance Sales jobs in Wisconsin are:

What are popular job titles related to Evening Insurance Sales jobs in Wisconsin?

For Evening Insurance Sales jobs in Wisconsin, the most frequently searched job titles are:

What cities in Wisconsin are hiring for Evening Insurance Sales jobs?

Cities in Wisconsin with the most Evening Insurance Sales job openings:

Infographic showing various Evening Insurance Sales job openings in Wisconsin as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 20% Part Time, and 5% Contract. Highlights an 84% Physical, 1% Hybrid, and 15% Remote job distribution.

LF Sales Rep

LeafHome

New Berlin, WI

$100K/yr

Contractor

Re-posted 23 days ago


Job description

LeafFilter Gutters and Gutterprotection

No cold calling- no sweepstake giveaway- real people confirming your leads.

Are you tired of cold calling looking for new business? Tired of the constant follow up, pay cuts, or unqualified leads? Tired of 3-5 hour meetings? LeafFilter by Leaf Home is North Americas largest direct to consumer entity and the largest home remodeling company in North America. LeafFilter pays the best rates, for less time in the field and less time in the home. If you are a sales PROFESSIONAL ready to be paid for your talents apply now and come join a team of the highest paid and most valued design consultants in home remodeling sales. We consider all applicants from all backgrounds, do not hesitate to apply. Some of our best consultants come from very different backgrounds, we have the training you need if you believe you have the talent!

Were looking for motivated sales professionals to join our highly successful sales force in the growing,home improvement industry. Our Design Consultants go to pre-scheduled appointments in residential homes and conduct sales presentations. They provide all of the necessary information for homeowners to make a same-day decision on their gutter protection needs.

Primary Responsibilities:

- Travel to and from your residence to company-generated, pre-qualified appointments with homeowners

- Perform product demonstrations and discuss custom quotes during in-home consultations

- Follow a value-based selling process embodying honesty and integrity

- Attend trainings and regular sales meetings

- Other duties as assigned

Qualifications:

- Hold a valid drivers license (required)

- Comfortable traveling up to 2 hours for appointments on a daily basis (required)

- Ability to lift and carry at least 20-60 lbs. of sample materials (required)

- Capable of navigating various applications on an iPad (required)

- Previous outside sales experience is not a requirement

- Willingness to learn a structured and proven sales process

- A strong desire and ability to close the sale

Compensation:

- Uncapped, full commission structure with current consultants earning $80,000-$220,000 plus.

- Performance-based bonus opportunities

- ICBA Contractors insurance offering

Schedule:

- Flexibility on a weekly basis

- Evening and weekend availability (required)

Job Type: Full-time

Compensation package:

  • Bonus opportunities
  • Commission only
  • Commission pay
  • Uncapped commission

Schedule:

  • Day shift
  • Evening shift
  • Monday to Saturday as needed